Dual Photocatalysis for the Straightforward Coupling of Thiosugars and Arylsulfoximines: Towards Unprecedented Cyclic Heteroatomic Structures. Issue 29 (22nd April 2022)

• Record Type: Journal Article
• Authors: Duhail, Thibaut; Zhu, Mingxiang; Rombault, Coralie; Dagousset, Guillaume; Messaoudi, Samir; Magnier, Emmanuel; Anselmi, Elsa
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 29(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-22
• Subjects: S-arylsulfoximines -- Dual photocatalysis -- Fluorine -- Heterocycles -- Thioglycosides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200173
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A general, scalable and easy to implement protocol is described for the coupling of thiosugars and various ortho ‐functionalized S‐aryl S‐perfluoroalkyl sulfoximines. This dual photocatalysis methodology was developed with a commercial hydrogen atom transfer reagent and produced key structures that were transformed into original cyclic skeletons bearing previously undescribed chemical functions. Abstract : A simple protocol towards thioglycosylated S‐aryl S‐perfluoroalkyl sulfoximines was developed. This coupling reaction between a series of glycosyl thiols and various ortho ‐functionalized S‐aryl S‐perfluoroalkyl sulfoximines employs the dual photoredox catalysts [Ru(bpy)3 ](PF6 )2 /Ni(II) irradiated with visible light. In addition, an unpreceded cyclization of the S‐trifluoromethyl substrates was discovered that furnishes original benzodithiazole and oxobenzodithiazole heterocycles.